Sodium Iodide → 2-Chloro-N-{4-[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)-pyrimidin-2-ylsulfanyl]-phenyl)-benzamide

HRID 473988Notes

Reaction equation

HRID 473988 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[N:19]=[C:18]([Cl:20])[CH:17]=[C:16](Cl)[N:15]=2)=[CH:9][CH:8]=1)=[O:5].[CH3:26][C:27]1[CH:28]=[C:29]([NH2:32])[NH:30][N:31]=1.[I-].[Na+].C(N(CC)C(C)C)(C)C>O.CN(C)C=O>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[N:19]=[C:18]([Cl:20])[CH:17]=[C:16]([NH:32][C:29]3[NH:30][N:31]=[C:27]([CH3:26])[CH:28]=3)[N:15]=2)=[CH:9][CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 594207972-Chloro-N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)benzamideHCID 178418690HCID 178418690, compound

Product 1

HCID 1784282252-Chloro-N-{4-[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)-pyrimidin-2-ylsulfanyl]-phenyl)-benzamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A 250 mL round bottom flask was charged with 2-chloro-N-[4-(4,6-dichloro-pyrimidin-2-ylsulfanyl)-phenyl]-benzamide (12.5 g, 30.4 mmol), 5-methyl-2H-pyrazol-3-ylamine (3.55 g, 36.5 mmol), sodium iodide (4.56 g, 30.4 mmol), N,N-diisopropylethylamine (6.9 mL, 40.0 mmol) and N,N-dimethylformamide (125 mL) under nitrogen. The reaction mixture was stirred at 90° C. for 5 h, then allowed to cool to room temperature. Water (600 mL) was added and the resulting suspension stirred at room temperature for 2 h and the solid collected by filtration and dried. The resulting white solid was triturated with hot ethyl acetate (50 mL), filtered and washed with ethyl acetate (1×20 mL) to give the title compound as a white solid (11.76 g, 82%). 1H NMR (DMSO): 2.16 (3H, s), 5.30 (1H, s), 6.48 (1H, s), 7.49-7.62 (6H, m), 7.89 (2H, m), 10.28 (1H, s), 10.84 (1H, s), 11.93 (1H, s); MS (ES+): 471.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe resulting suspension stirred at room temperature for 2 h
  3. filtrationthe solid collected by filtration
  4. customdried
  5. customThe resulting white solid was triturated with hot ethyl acetate (50 mL)
  6. filtrationfiltered
  7. washwashed with ethyl acetate (1×20 mL)

Sources & evidence

ORD record
ord-acba3acb8c8042dba223f6dddca55f2d
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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